Tetrabutylammonium Fluoride → HCID 59375124, compound

Participants

Reaction Steps

Step 4 A solution of 7-(1-(tert-butyldimethylsilyloxy)cyclopropyl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide (0.039 g, 0.065 mmol) in THF (0.66 mL) was treated with tetra-n-butylammonium fluoride (1 M in THF, 0.098 mL, 0.098 mmol). After 10 min, the mixture was combined with an identical reaction mixture done on 22% of the scale described, and the mixture was concentrated. The residue was purified by preparative HPLC. The appropriate effluent fractions were treated with NaHCO3 (aq) and partially concentrated. The aqueous residue was extracted three times with DCM and the combined organic phases were dried and concentrated to give 7-(1-hydroxycyclopropyl)-4-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-9H-carbazole-1-carboxamide as a white solid (23.3 mg, 60%). 1H NMR (500 MHz, DMSO-d6) δ 11.42 (1H, s), 8.18 (1H, br. s.), 7.98 (1H, d, J=7.7 Hz), 7.80 (1H, d, J=7.7 Hz), 7.72 (1H, s), 7.68 (2H, d, J=3.8 Hz), 7.60 (1H, d, J=7.7 Hz), 7.56 (1H, ddd, J=7.8, 4.1, 4.0 Hz), 7.49 (2H, t, J=7.7 Hz), 7.33 (1H, d, J=7.1 Hz), 7.01 (1H, d, J=7.7 Hz), 6.95 (1H, d, J=8.2 Hz), 6.79 (1H, d, J=8.2 Hz), 5.95 (1H, s), 4.90-5.02 (2H, m), 1.84 (3H, s), 1.07-1.15 (2H, m), 0.91-1.00 (2H, m). Mass spectrum m/z 488.3 (M+H)+.

Provenance & Evidence